


Lesson of Defeat

by Humanitysfandomhoe



Category: Assassination Classroom
Genre: Abuse of Authority, F/M, Fucking Machines, NSFW, No Aftercare, Rape, inappropriate work relationship, noncon
Language: English
Status: Completed
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-16 17:13:51
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,306
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28834692
Author URL: https://archiveofourown.org/users/Humanitysfandomhoe/pseuds/Humanitysfandomhoe
Summary: Asano Gakuho is not a forgiving man and his methods of reform are unconventional to say the least. To make a mistake as his secretary is unacceptable and you will pay the price ...
Relationships: Asano /reader, Asano Gakuho/reader
Comments: 3
Kudos: 15





	Lesson of Defeat

**Author's Note:**

> TW: Dubcon/noncon, no aftercare, fucking machine, power abuse, overstimulation, inappropriate work relationships.

As Asano Gakuho’s secretary, much was expected from you and the slightest error would be met with cruel and unyielding action. You never knew what to expect from the cold and calculating man but you knew it would leave you a broken mess(whether it be physically or emotionally) until he decided to put you back together again. You try, you really try to do everything perfectly, to do your job well but you always manage to fall short. That’s how you ended up in this predicament, ankles, and wrists bound to the legs of his large mahogany desk, leaving you completely vulnerable. A thousand thoughts bounce around your head, none of them good. What was he going to do? Hit you? Spank you? Violate you? You hated to admit the idea of him stuffing your pussy with his fat cock wasn’t completely unappealing, or that you had thought about it on more than one occasion as you daydreamed instead of doing your job. Your wrists and ankles ached and your short skirt was beginning to hike up, wiggling only made it worse and you were certain the curve of your ass was visible now. How utterly embarrassing to have your boss see your ass clad in a pair of unflattering panties. He must find you disgusting, pathetic even. He stands there and lets you squirm without saying a word, his cold red eyes trained on you in a way that makes your skin crawl. It feels as though hours have passed when he finally speaks.  
“I’m sure you’re thinking that I am being too hard on you,” Asano states as he thoughtfully strokes his chin, “ but the fact of the matter is that if you want to continue here, you must learn.”

He pushes himself off of the wall reaching above his bookshelf and taking down a long leather riding crop. “How can I hold my students to such high standards while my staff dawdles on their phones, hmm? Does that seem fair to you?”

You can feel his leather riding crop stroke against your inner thigh, slow and gentle, making goosebumps grow across your skin as he speaks, a silent warning as to what would come next. The tension builds and builds as he stares down at you with that cold face, examining you like a bug on the wall when his threat is acted upon as he brings it down sharply against your soft thigh and you cry out sharply. There’s no doubt that you’ll have an ugly bruise later on but right now that is the least of your concerns. Your sounds clearly annoy the principal whose face sours, a low grumble leaving his lips as he flips your skirt over and unceremoniously yanks your panties down before stuffing them into your mouth.  
“If you wish to be made an example of just say so and it can be arranged since you seem to want all the world to hear you.” Asano threatens, grabbing a fistful of hair and yanks your head upwards.  
The only thing you can do is shake your head, looking at him with wide eyes in a silent plea for a small mercy. Still unsure of exactly what you want, you certainly couldn’t let your coworkers hear you like this or worse the children because even though you disagreed with Asanos methods you believed in doing everything you can for these kids to grow and become their best selves. If that meant suffering this humiliation in silence, so be it.

“As I thought.” The principal sneers, walking away and disappearing into a connecting room to his office, the one you were not allowed to enter under any circumstances. You can hear the sound of something on wheels being pushed towards the doorway, something heavy. Pretty eyes widen as the contraption rolls into view, a colossal machine put together with simple parts, if you were standing it would stop a little higher than your hips. But its size and stature aren’t what intimidates you, it's the painfully large and thick dildo strapped to the end of it that has you aching to snap your legs closed. Not even in your wildest imagination did you think that THIS would be your punishment.  
"S-sir, I don’t understand. " You sputter, looking to him for some reassurance that this was all a joke.  
He chuckles cruelly as he wheels it behind you, the large head of it prodding at your ass. "Perhaps not, but you soon will. " He assures, lifting your ass a little higher to line the thing up with your pussy.  
"I'm not inherently cruel," Asano informs as he pulls out a small vibrating wand. "I won’t allow you to tear."  
You're not sure what he means, you don't even have time to think as the sleek toy presses to your clit, a muffled moan leaves your lips as he presses down hard and lights up every nerve on the little bud. In response your body jerks, hips swaying back and forth, anything to get away from this overwhelming pleasure being forced onto you too hard and too fast. It’s painfully obvious that you don’t take care of yourself properly when you’re already cumming within seconds He doesn’t pull it away after your first orgasm or even the second, he keeps the buzzing head against your little clit until that pussy is drooling and making a mess of his floors. Even with all the slick coating your pussy, the dildo has a hard time fitting inside your hole. The push is slow, slipping past the hole several times before Asano is forced to reach down there himself and push the blunt head in himself. You whimper and tell him it's too much but he won’t listen, continue to push the thick shaft further into your pussy until it can’t anymore. You cry out when you feel it knock against the wall of your cervix at which your principal scoffs, obviously displeased that you couldn’t take it all. Even with something so simple you still manage to disappoint him.

The machine whirls to life, sounds of gears turn as the artificial cock withdraws and gives you a feeling of relief as it does so, your pussy instantly attempting to squeeze closed again. That relief is short-lived, the breath knocked from you as it goes rocketing back into you and makes you see stars. Over and over again it pounds into your poor pussy, the little ridges at the top constantly stroking your g-spot as it goes in and out.

You whimper, begging your boss to turn off the machinery, swearing that you had learned your lesson that you would be his perfect secretary from now on. Asano knew better, he knew that if he let you off before the lesson was done you'd make the same mistake the same as with his students. If a lesson isn’t seen through to its completion the student would never learn. He doesn’t enjoy tormenting you. He doesn’t think you look so cute taking a cock that's too big for you with tears streaming down your cheeks as your mouth hangs open, a steady stream of drool slowly stretches it's way to the floor as your body bounces in time with the mechanic thrusts. He doesn’t enjoy this at all.  
His firm hand comes down to rest on the top of your head, fingers gently stroking your scalp as you continue to be pounded into oblivion, a small comfort that you relish deeply. It drifts down, the back of it stroking against your cheek to grip your chin, the pad of his thumb strokes against your damp bottom lip, cold red eyes staring into your blank ones. The smile he gives you is oddly warm even if it doesn’t reach his eyes as he reaches into his slacks, pulling out his fully erect cock. Nowhere near as large as the cock inside you but still impressive nonetheless with a pretty red head dripping with precum and veins running down the underside. He taps the heavy head against your lip urging you to open your mouth and take him in.

“Maybe if you suck my cock like a good slutty secretary, I’ll turn it off.”  
You’re whining at the cold look he’s giving you, knowing that whether he’s lying or not sucking him off was not an option. Your mouth opens with hesitation, the space barely enough for him to fit making him scowl dangerously.  
“You’ll either suck my cock like you mean it or not at all. I can just leave you here on this machine and come back for you in the morning. How would you like that? Maybe the janitors will come in to clean and find you like this, pathetic and vulnerable there’s no way they could resist reaming you.”

Tears begin to well again as you adamantly shake your head as you open your mouth, sticking out your tongue as a desperate offering. Asano smirks in approval, petting your head like a puppy as he slowly slides his cock over your tongue.

“Good girl.” He praises, watching as you hollow out your cheeks around the head of his cock. “Good little slut.”  
His hips begin to thrust lightly as you suck, letting you set the pass as he busies himself with watching you get pounded from behind. You can barely focus on anything besides mindlessly suckling on his cock as the machine continues to slam into your cunt., the cheeks of your ass bouncing with every thrust and giving your principal a good show. After a while, your mindless sucking no longer satisfies him and you’re given no warning before you have a fat cock popping past the small opening of your throat. Your eyes widen, staring up at him with an expression of betrayal.

“Don’t look at me like that.” He chuckles cruelly as he pulls back out. “I was never going to be able to cum with those pathetic sucks you were giving me.  
A sick gurgling sound fills the room as he slams back into your mouth in time with the machine, your nose pressed against his dark vermillion pubes. He treats you with an utter lack of care, grabbing fistfuls of your hair like handles as he pushes his cock right down that tight throat. It’s so small, contracting around his throat like the perfect little fleshlight, the miserable expression on your face making it that much better. Perhaps this did go beyond simple discipline, perhaps Asano did enjoy watching you suffer but he worked hard all day every day, and did everything to make this school the very top in the nation. He deserved some stress relief.

The constant pistoning of the XL dildo in your pussy soon overcomes you, your orgasm hitting harder than you’ve ever experienced. Even against the tight ropes and unyielding wood of his desk your body manages to contort as it comes, causing the cock to slip out of your hole as you scream. Asano frowns, about to reach over and force it to go back in when he sees the perfect position it’s in. the machine continues to move as if it were still fucking inside your hole, your orgasm prolonged as the slick soaked appendix strokes against your clit faster than any human fingers ever could. He pulls out his cock from your mouth, allowing you to fruitlessly beg him to make it stop.

“No, no!” You sob, craning to look over your shoulder as you try to angle your clit away. “ Please sir, I can’t, it’s too much. Too much.”

Asano smirks, squeezing your cheeks in his big hand and forces your lips to pucker. “I decide what’s too much.”  
He forces you to maintain eye contact with him as your orgasm is stretched out, eyes rolling back until only the whites of them are visible as your lashes flutter. It's clear that he takes far too much pleasure in watching you suffer. You just look so cute like this tear sustained face, raw lips, and snot dripping from your nose, an absolute masterpiece. Now all he needed to do was sign his work. he holds your face in place with one hand the other a blur as he jacks off his cock to your absolutely wrecked expression, the only sign that he’s getting worked up is the slight sheen of sweat at his hairline while his face is a brick wall. Asano’s balls clench as you babble apologies to him, calling him your master, promising to never disappoint him ever again, and just like that he’s a goner. He gives a muffled grunt as his balls tighten and his cock spurts out rope after rope of cum. It splatters onto your face, clumping your lashes together and occupying every available crevice. You sob in utter humiliation, head dropping in shame as he stumbles back, leaning against the ball to catch his breath and stop the trembling of his legs.  
Once he’s gained control Asano rounds the wide mahogany table, reluctantly turning off the machine. He crouches for a moment, marveling at how raw and stretched your pussy is, it clenches when he blows gently on it and forces slick to drip out, adding to the pool already on the floor. Beautiful. He unties you, coming to crouch in front of your face, and slaps you out of your daze. He waits until the clouds in your eyes thin and focuses on his before giving you your orders.

“Clean yourself up, I want this office spotless when I arrive in the morning, is that understood?”

“Yeth sir.” You slur, weakly attempting to pick yourself up, and helplessly fall back onto the desk.

“Good.” is the last thing he says to you before leaving you to struggle on your own.


End file.
